3,3-diethoxyprop-1-ene

• ChemBase ID: 108717
• Molecular Formular: C7H14O2
• Molecular Mass: 130.18486
• Monoisotopic Mass: 130.09937969
• SMILES: CCOC(OCC)C=C
• Canonical SMILES: CCOC(OCC)C=C
• InChI: InChI=1S/C7H14O2/c1-4-7(8-5-2)9-6-3/h4,7H,1,5-6H2,2-3H3
• InChIKey: MCIPQLOKVXSHTD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3,3-diethoxyprop-1-ene
• IUPAC Traditional name: 1-propene, 3,3-diethoxy-
• Synonyms: 3,3-Diethoxy-1-propene; ACROLEIN DIETHYLACETAL; 3,3-diethoxyprop-1-ene; Acrolein diethyl acetal; 3,3-二乙氧基丙烯; 丙烯醛缩二乙醇

Database IDs

• CAS Number: 3054-95-3
• EC Number: 221-276-0
• MDL Number: MFCD00009239
• Beilstein Number: 1701567
• PubChem SID: 162094607; 24845184; 24890652
• PubChem CID: 62477

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 1.8483177
• LogD (pH = 7.4): 1.8483177
• Log P: 1.8483177
• Molar Refractivity: 37.4535 cm^3
• Polarizability: 14.764178 Å^3
• Polar Surface Area: 18.46 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Boiling Point: 124-125°C; 125 °C(lit.)
• Flash Point: 13°C(55°F); 15 °C; 59 °F
• Density: 0.852; 0.854 g/mL at 25 °C(lit.)
• Refractive Index: 1.4010; n20/D 1.398(lit.); n20/D 1.402

Safety Information

• RTECS: AS1370000
• European Hazard Symbols: Flammable (F); Irritant (Xi)
• UN Number: 2374; UN2374
• German water hazard class: 3
• Hazard Class: 3
• Packing Group: 2; II
• Risk Statements: 11-36
• Safety Statements: 9-16-26-33
• TSCA Listed: 否
• GHS Pictograms: GHS02; GHS07
• GHS Signal Word: Danger
• GHS Hazard statements: H225-H319
• GHS Precautionary statements: P210-P241-P303+P361+P353-P305+P351+P338-P403+P235-P501A; P210-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 2374 3/PG 2
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95.0% (GC); 96%
• Grade: purum
• Linear Formula: CH2=CHCH(OCH2CH3)2

DETAILS

MP Biomedicals - 05208456

MP Biomedicals Rare Chemical collection

Sigma Aldrich - A24001

Packaging
25, 100 g in glass bottle

REFERENCES

• Protected acrolein equivalent. Reacts with Grignard reagents (CuBr catalysis) to give predominantly (Z)-enol ethers which can be hydrolyzed to 3-substituted propionaldehydes: Tetrahedron Lett., 3833 (1975). The (E)-enol ether is formed selectively with a Ni(II)-phosphine catalyst: Chem. Lett., 351 (1985).
• Heck coupling (see Palladium(II) acetate, 10516) occurs with aryl or vinyl bromides in the presence of morpholine or piperidine: J. Org. Chem., 46, 1061 (1981); J. Chem. Soc., Perkin 1, 2597 (1987):
  
• In the presence of acid, generates the ethoxyallyl cation which is a powerful dienophile, undergoing Diels-Alder reactions at low temperatures: J. Am. Chem. Soc., 109, 2182 (1987).